Caroline Taylor's heart fills with pain as she stares at the decrepit houses on Indian Road and thinks back to her childhood. 

"I played with kids in here," says Taylor, gesturing at a home with boarded-up windows as transport trucks rattle along the Ambassador Bridge looming high above.

This week, the homes her friends lived in, and the memories they made there, are being demolished after a decade of protests, neglect and legal battles that wound all the way to the Supreme Court of Canada.

One battle remains unresolved. A judgment is pending in a $16.5-million class action suit filed by residents who likened to a "war zone" the rows of dilapidated homes in the shadow of the bridge.

The homes are finally coming down because the company that owns the Ambassador Bridge is moving ahead with a six-lane, $1-billion replacement span after receiving approval from the federal government in late August. 

"I can't believe it's actually happening," says Taylor as an excavator rips through the roof of a vacant, red-bricked house, the first of 33 homes set to be torn down. 

Bridge Headline

A storied community sits in the shadow of a billion dollar bridge project in Windsor. (Chris Ensing/CBC)

Behind the home and across the street sits a gray, cement on-ramp along a back alley. It runs next to the existing bridge but ends abruptly in mid-air, waiting to be connected to a second span. Residents of Windsor's historic Sandwich Towne have been eyeing that on-ramp for years, suspicious of the bridge backed by an American billionaire they have come to distrust.  

"I'm feeling some tension, and I'm feeling some fear," says Taylor.

The company has made recent overtures in Sandwich Towne and promises to be a better community partner, but Taylor worries about the company's record of litigation and the reliability of its pledges.

"They can not be trusted," says Taylor. "They have made enemies with the municipal governments, the provincial governments and the state governments on both sides of the border."

Conditional Approval 

The Canadian government's approval of the replacement span came with a long list of conditions the company has to satisfy, including community improvements, the destruction of those dilapidated homes and the eventual demolition of the existing bridge. 

"The conditions are very set in place," saysTerrence Kennedy, a long time Sandwich Towne resident who describes himself as an advocate for the community. 

Terrence Kennedy

Terrence Kennedy is worried that the construction of a replacement span will disturb sacred grounds in Sandwich Towne. (Chris Ensing/CBC)

The bridge company must start building the replacement bridge in five years and demolish the existing bridge within five years of the new span opening. The company must also construct a new fire hall, develop and maintain parkland in the area and consult with Walpole Island First Nation.

Kennedy says the area on which the span will be built is sacred ground. 

"This is all First Nations land," says Kennedy.

"We know that there's bones out there. We know that there's artifacts out there."

​'Losing its fragrance'

The demolition of the first homes along Indian Road represents the end of an era in Sandwich Towne and the fight between the bridge company, residents and the city.

The bridge company bought up dozens of homes and allowed them to rot in what critics called 'blockbusting.' The city crafted a Sandwich-specific bylaw requiring special dispensation to tear down any homes in Sandwich Towne and rebuffed repeated attempts by the bridge to tear down the homes, despite arsons, vandalism and reports of vermin infestations.

The city feared the bridge would tear down the homes and build a second span. City officials now say they have no choice but to allow the demolitions because the federal permit to build the replacement span stipulates they be razed.

It's a development that has Taylor feeling anxious.

Caroline Tayor0:51

"I know these houses are a mess to look at," says Taylor. "But like I say, 'Better the devil that you know than the one that you don't.'"

She worries that when the houses come down, the streets under the Ambassador Bridge will be closed for long stretches to build the project — cutting Sandwich Towne off from the University of Windsor and Riverside Drive. 

"It's losing its fragrance, almost," says Taylor.

Bridge Company Responds

Bridge company president Dan Stamper tells CBC News the company is committed to the conditions laid out by the federal government and plans to soon open a storefront to assuage concerns in Sandwich Towne.

He says the company has a "bad rap" after years of fighting between varying levels of government on both sides of the border. 

"Have we done some things wrong? Yes. Has the government done some things wrong? Yes. The good news now I think we're all on the same page," says Stamper. 

Bridge Demolition0:36

Stamper says community concerns about a massive truck plaza are overblown.

"The truth is it's about six and a half or seven acres," says Stamper. "It's already part of the bridge plaza so we're not going to be extending into the community."

The size and placement of the truck yard is because Canada Customs wants to relocate the truck inspection station, he says.

Phased demolition

The bridge company is applying for demolition permits in three phases. 

Here's how it will roll out.

Demolition Phases0:29